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Smoking a good cigar can be one of life’s great joys.  It can also be a little intimidating for a beginner.  When I started out I had to endure several long months of trial and painful error.  I hope you can avoid that. 

**NOTES: This article is a little long.  Therefore, I’ve divided it into sections with bold caption headings.  If you have a question about a particular subject, just scroll down until you see it.  Of course, I think the story is worth reading in its entirety.

Also, this is a guide to proper cigar smoking, not a guide to cigars (I do briefly touch on some common elements though).  My aim here is to educate readers about the how-to’s of the cigar world.  I leave picking a stick to you, your imagination, and your local tobacconist.**


And now, here’s some cigar advice:

Finding a Cigar Shop

First, you need to find a good cigar shop.  For an idea of what a great shop is, re-read my column in praise of my local tobacconist: Top Shelf Cigars, https://perrinlovett.wordpress.com/2013/03/03/top-shelf-cigars/.  Try to emulate that, if you can. 


(Where the smoke “just pours out!”)

Gas stations, drugstores, and super-markets sell cigars (some of them have a decent selection too).  However, to get the most out of the experience one must venture into an establishment dedicated to the sale of tobacco – fine tobacco, not a cigarette outlet.  There are also cigar outlets – avoid them if possible.  You want a decent place with several hundred “facings” (types of cigars to choose from) and a comfortable lounge for smoking in (preferably complete with several happy regular customers).

In addition to places that sell food, medicine, and Marlboros, here are some other things to avoid.  If you enter a shop, ask for help, and they tell you a membership or fee is required to smoke therein – leave.  If the place is full of stoned-looking reprobates – leave.  They are stoned and not from good tobacco.  If a U.S. retailer hawks “Cuban” cigars at their shop – don’t even bother.  They’re either lying or breaking the law.  If you walk in and see a bunch of odd-shaped glass pipes – leave, it’s a head shop.  I hate to list this one for fear of..oh heck… if the shop is populated by children, women, and/or teenagers, then it’s not going to be a good time.  By and large, cigars are for men.  There, I said it.

Picking the Perfect Cigar (For You)

Once you find a good shop, you need to pick out a good cigar.  Any place worth its smoke will have a knowledgeable staff who can assist you with your purchase.  Beginners traditionally stick with lighter, milder sticks to start with.  Something strong enough for a veteran may send a newbie to the bathroom for a prayer at the porcelain altar.  Beware.  Also, it helps to eat something first.  Go try the new hobby on a Saturday after lunch or dinner.  Be prepared to devote at least an hour to the smoking alone.  Picking the right stick can take a while in addition – set aside two hours to do it right.  Smoking with a friend helps too though you’re likely to make friends out of the regulars.  I’ve never had any trouble striking up or joining a conversation at any shop I’ve visited.  Cigar enthusiasts are nice people. 


(A well-stocked humidor.)

By the way, good cigars are no necessarily cheap, though not outrageously priced.  Be prepared to spend at least $5-10 for a decent stick these days; boxes of 20-25 run over $100 – don’t buy boxes until you really know what you want.  Good shops keep their cigars in a walk-in (or large cabinet) humidor.  This is to control the temperature and humidity of the sticks.  The general rule is 70/70 or seventy degrees farenheit and seventy percent relative humidity.  Slight variations are acceptable.  You will get used to the feel of a humidor.  I can walk in and tell if everything is kosher.  For the novice, look around and you will find a set of gauges somewhere.  Make sure their readings are close to 70/70.  If the sticks are too cold or dry they will crack and ruin the experience.  If they get to warm or wet bad things can happen – remember the movie Gremlins?  If their humidor is off and the staff doesn’t pre-emptively apologize and explain it’s a freak problem, you should probably move on.  Also, if you inspect a stick and see little things moving on it that look like bugs, they are.  Cigar beatles to be exact.  Time to leave.

Speaking of appearances, you will notice immediately a wide variety of shapes, sizes, colors, and titles.  The color, texture, and dry versus oily appearance have to do with the type of tobacco and the way it is presented or manufactured.  Most of these babies are hand-crafted by skilled personnel in the Dominican Republic, Nicaragua, Honduras, or elsewhere.  Some cigars are square due to being “box pressed” or formed inside a squared off mold.  I don’t like those as a rule, you might love them.

Cigars are generally three parts: the “filler” is the core tobacco inside; the “binder” encases the filler; the “wrapper” is the pretty piece of tobacco on the outside.  Look for a wrapper without too many visible veins (it’s a leaf after all), cracks, or other imperfections.  Look for smoothness and consistency.

The shade of the tobacco is usually somewhat indicative of its “strength” or the intensity of the taste.  Darker generally means full-bodied and stronger, though not always.  I recommend a lighter (natural or Connecticut) wrapper cigar for starters in a medium size.  Cigars are measured length by ring gauge (width).  Ring gauge is a function of 64ths of an inch.  Thus, a 6×60 cigar is six inches long with a diameter a little less than an inch.  That’s a big cigar (I’m finishing off a GIANT 7×70 right now), go for something a bit smaller.  I’ll leave size descriptions and names to the local tobacconist along with explanations of the tobacco in the stick and where it’s from. 

When judging a cigar in the humidor, very gently squeeze it between your thumb and forefinger.  If it’s rock hard you will have a hard time puffing and keeping it lit.  Too soft and it may burn too fast.  Uneven feel may mean an uneven burn and necessitate regular touch-ups with fire.  Sometimes these issues can’t be avoided, even the best sticks may have a bad lot.  If you have horrible problems (splitting, grossly uneven burn, or an inability to draw smoke from fire to mouth, see the owner/staff.  A good shop will replace a problem stick.  If they give you a hard time, it may be time to leave. 

A final word about stick picking: find what you like.  This will mean some experimentation.  Start with general recommendations but gauge all cigars by how happy they make you.  There are several major publications which rate and review cigars.  These can be good sources of information.  Just remember, they usually require advertising or fees for their reviews.  And, they come up with some of the most convoluted taste formulas imaginable.  I really never pick up on notes of pencil lead, moss, cinnamon, or garlic or whatever.  I smoke for the taste of tobacco; I like what I like.  Follow that rule.

A final, final word about taste: some cigars are flavored – naturally and artificially.  Seasoned pros tend to shy away from these.  You should too in the beginning.  If you discover you love them, stick with them, and be prepared for some teasing…

Prepping the Cigar

Okay, you’ve found a comfy, friendly location and the perfect starter stick.  You’re almost ready to start enjoying, but not just yet.  First, you must perform a little preparation.  Almost all individual cigars come wrapped in cellophane.  Some come in glass or metal tubes, some come in paper boxes and some in fancy little wooden boxes.  Obviously, a cigar must be extricated from its tube or box prior to lighting.  So to, must a stick be freed from its cellophane.  I’ve seen too many people cut the cigar while it’s still wrapped.  Don’t do that, it’s just tacky.  The plastic comes off easily, usually in one fluid movement although some are closed off by a little paper sticker.  Just tear the sticker and open her up.

Unlike a fine wine, a fine cigar does not need to breathe before being enjoyed.  It does require proper cutting and lighting though.  Professionals have their own ways of accomplishing these important prerequisites as unique as they are.  Many of the old hands who actually make the sticks are known to simply bite the cap (the rounded end of the wrapper) off and light with a regular old Bic lighter.  That works fine and I’ve none it myself but I’m here about etiquette today, I’ll act like it. 

Cigar cutters are specialized tools designed to leave a clean-cut.  Punches are just that, they punch little holes in the cap for smoke to exit through.  They don’t work well on tapered or pyramid type cigars.  I don’t use them – personal habits.  V-cutters make a …. yep, “v” shaped grove in the cap.  I don’t really care for those either.  I like a full opening at the end for full smoke and taste delivery.  I use a guillotine cutter.  This device has two semi-circular bladed that converge together to shear off the end of the cap.  Some have only one blade, two generally work better.  Some are scissor-like, others are pressed together in a straight line without a hinged angle, others are actually little versions of that dreaded device from the French Revolution – for cigars, not nobility.  Watch your fingers, please.  On a regular, rounded cap, just cut off about 1/8th of an inch; for tapered designs, try half an inch or so.

Cigars can be lit by just about any source of sufficient heat.  Matches, Bics, Zippos, butane torches, camp fires, and stove elements all do the job.  Most reputable shops will have a selection of modern lighters in their lounge area.  Some purists shun gas-powered lighters period, claiming they impart a petroleum taste.  I don’t recall ever being bothered by this, you likely won’t either; I had to mention it though.  The prim and proper way to light is to use any source to first ignite a slender strip of cedar (on hand in good shops), the cedar then lights the cigar – and makes an ashy mess.  They really classic way to light was taught yours truly by an old Cuban doctor for whom I had the gravest respect, it is as follows:  lightly toast the foot of the cigar (open end, opposite the cap) BEFORE clipping the cap.  Just char it slightly.  Then cut the cap.  Then light with cedar.  This supposedly preps the cigar for optimum smoke-ability and flavor. 

Lighting the Cigar

However you get there and whatever you use, eventually the fire will meet the leaf.  “Toasting” is always a good first step to heat up the 70 degree end.  Keep it light, watch carefully so that you don’t start a fire up part of the wrapper and binder.  Concentrate all firepower on the foot!  Speaking of, lighters these days can come with two, three, even four or five flame jets.  These will light a stick instantaneously or cut steel.  Beginners would do well to stick with one jet or flame for precision. 

Once your cigar is adequately toasted – judged by eye, then it’s time to fire it up!  Put the cool end in your mouth (don’t bite down – loose and gentle) and take a few slow, long draws while firing the other end at the same time.  Rotate the cigar with your fingers while lighting in order to assure an even light.  It’s quite normal for open flames to come from the end, they die out almost at once.  After several turns and good puffs, take a look at the burning end.  It should be red evenly across the entire foot.  Touch up as needed.  Be mindful to only return the cool cap end to your mouth.  I’ve done it the other way and it’s not pleasant!


Now that the little beauty is lit, you can sit back and enjoy.  Take it slow and easy.  I am frequently accused of huffing and puffing my sticks like the Big Bad Wolf.  A quality cigar will continue to smolder for about five minutes after you draw on it.  If it goes out, you are going too slow.  Re-lighting can tarnish the taste with a bitter or stale flavor for a second.  It’s not horrible but should be avoided.  Take regular draws. 

Larger sticks may require a double puff to fully extract the right amount of smoke.  That smoke should be contained in the mouth.  Let it circle around as you would a good wine or whiskey.  As it passes over the different areas of your tongue you will taste the various elements of the tobacco.  This is a genuinely delightful process.  Enjoy it as you would a good massage or a great steak or other delight.  The tastes may change as the cigar burns or they make remain even throughout.  Blow out once the taste subsides.  You can keep the stick in mouth or hold it and look at it in wonder. 


(Don’t he look happy?)

Cigars are not cigarettes.  Do not attempt to inhale the smoke as it is a little stronger than what you’re used to and can sear the lungs most unpleasantly.  Cigars are meant to be enjoyed for their flavor.  Absorb it.  You will also absorb nicotine; if you find yourself dizzy, back off a little.  A little buzz is fun, getting sick is not.  Also, a little ash is great to look at, a large ash is looking for somewhere to fall.  Dump the old ash at intervals to keep it from falling on your lap; try it every inch or so.

Ashes to Ashes

When, sadly, the cigar is done, one must part with it.  Some will smoke right down to a nub, until their fingers are singed.  I recommend stopping when there’s about an inch to an inch and one-half left, about where the “band” is or was.  The band is the cigar’s label, usually very intricate and decorative.  You may leave a band on while smoking, remove it before lighting, or take it off once the stick is going.  Bands that sit too high need to be either removed or pushed down a bit.  You want your lips on the leaf only.  If you move or peel off the band, do so with care.  The band is a paper ring, closed on itself with a little dab of glue. 

Sometimes the band is really tight, sometimes a little glue gets on the leaf and secures the label in place.  The glue is a natural non-toxic plant material and won’t hurt you or the cigar.  However, if ripped off forcefully, it can take part of the wrapper with it.  Finesse is the key here.  If it doesn’t budge with ease, leave it in place.  As the fire approaches it will loosen up and then is easy to remove.  Do not smoke the band!  Not unless you like the added taste of burned paper!

When the cigar is done, just lay it in an ashtray.  Don’t try to crush it out as this can cause flare-ups and an abundance of smoke which soon grows stale and stagnant.  An active cigar produces wonderful smelling smoke.  You may find yourself enjoying it second-hand.  Stale smoke is, well, stale.

Meet the Regulars!

While you smoke, feel free to interact with those around you.  Cigar shops are always the home of interesting men of many different walks of life.  Join a conversation!  If you’re new, they will likely want to know all about you.  Have fun and make friends!


 (Join the fun!)

The shop is an ideal place to get away and enjoy your free time.  Not free?  Bring a little work with you.  In addition to smoking and talking, men find the lounge a great place to check emails, read, or write.  I’ve crafted some of my best blog columns at Top Shelf Cigars.  I’ve even met clients there.  Keep the phone conversations to a minimum.  If you must field a call it’s best to do it outside the lounge.  While friendly, regulars are not nosey and don’t care to hear you talk to the wife or the boss.  It’s a shame I have to mention this, but mind your manners in shop.  Rude or obnoxious behavior will not only make you a pariah, it can get you ejected as well.  Remember, it’s a happy place for respectful adults.  No-one likes a jerk or a know-it-all.  I’ve seen idiots bounced out.  Don’t be “that guy.”  Once you’re “initiated” into the regulars you will find out the personality of the place – usually collegiate with lots of good-natured humor.  Thin skin usually isn’t well suited for lounging!

Cigars at Home

You can, of course, enjoy your smoke in the comfort of your home.  Usually, with a wife and kids, that means out back, on the porch, or in the garage.  I’m in the garage right now.  Take the opportunity to create your own little cigar lounge!  A chair, an ashtray, a cutter and lighter is all you need.  Add a little fire pit or a radio and you’re in cigar heaven.

Smoke on the Road

The car can be a great place to smoke, particularly on longer trips.  Keep a window cracked or down to avoid a buildup of stale smoke and to maintain road visibility.  You may need to freshen the interior up from time to time as well.  Be mindful that when you smoke the smoke gets in your clothes and can stay there.  The people in your upcoming meeting may not appreciate it.  The taste of smoke will also linger in your mouth and on your breath.  You will get used to it but brushing or a little gum or mints will go a long way towards societal interaction post smoke.  Bear in mind that in the tight confines of an auto, falling ashes will make a greater mess, and one harder to clean up.  Falling embers (happens with the best sticks) can mean a hole burned in your pants or shirt.  Take precautions as needed.

Public Relations

Cigars can be fun just about anywhere.  They make yard work less tedious.  They go naturally with a fishing trip.  They can help one relax at the beach or in the mountains.  I love strolling along behind my family on vacations, puffing away carefree.  If I do have a care, it’s not to offend the non-cigar public.  Oddly, not everyone likes cigar smoke.  Be mindful of others and try as best you can to shield them from what they might find offensive.  Don’t go out of your way but exercise a little curtsey.  All cigar lovers benefit from good public relations.


(Cigar in the park on a cool fall day.  Ahhhh.)

Cigars on the Rocks (Drinks and Smokes)

In the comfort of your home man cave or the comfort of your home away from home, you may decide to pair a cigar with a suitable adult beverage.  You want something that accentuates the taste of the stick, without drowning it out.  Different cigars go well with different drinks – from Sprite to red wine.  Usually I partake of either a dark ale or a short bit of single-malt Scotch whiskey.  There’s no set formula.  Again, you have to find what works best for you.  As I’m typing here in the garage, I’m still smoking that beast of a 7×70.  It’s a slightly stronger than average stick so I have paired it with The Duck-Rabbit’s Wee Heavy Scotch Style Ale – dark and strong (8% abv).  Don’t let the drink overwhelm the smoke.  A sip here and there between puffs adds a lot of enjoyment.  Slamming glass after glass of 80-proof bourbon just gets you drunk – unless that’s your plan!  I judge not, just offering my advice here.

Smoke Time!

Finally, I’d like to touch on when to smoke.  The best answer is: whenever you feel like it and have the time.  A Saturday morning cigar with coffee and the paper makes for a great time.  After a long hard week, a friday night smoke is most relaxing.  I know men who literally smoke from sunrise til sunset.  Do what works best for you.


In doing your best with cigars you will join some of the greatest men in history.  Mark Twain, Winston Churchill, and George Burns were avid cigar enthusiasts.  Join them and your contemporaries in a great past time.  Remember always your Kipling: “A good cigar is a smoke.”


(Don’t mess with Winston.  Google.)